The self-assembly and dynamic properties of thiophene-containing [2]catenanes

P. R. Ashton; J. A. Preece; J. F. Stoddart; M. S. Tolley; A. J P White; D. J. Williams

doi:10.1055/s-1994-25692

The self-assembly and dynamic properties of thiophene-containing [2]catenanes

P. R. Ashton, J. A. Preece, J. F. Stoddart^*, M. S. Tolley, A. J P White, D. J. Williams

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

The template-directed syntheses of two novel [2]catenanes, incorporating bisparaphenylene-34-crown-10 interlocked with tetracationic cyclophanes, containing either one or two 2,5-disubstituted thiophene residues in addition to two bipyridinium units, are reported. The X-ray crystal structures of one of these [2]catenanes and of its component tetracationic cyclophane are reported. The former exhibits short [S···O] contacts in addition to the expected π-π and [C-H···O] stabilising interactions. Dynamic ¹H NMR spectroscopy has revealed that there is a substantial degree of order which characterises the molecular structures of both these [2]catenanes in solution at a noncovalent bonding level. Identifying and understanding these noncovalent bonding interactions between the molecular components are crucial to the design of catenanes that will self-assemble in a highly efficient manner.

Original language	English (US)
Pages (from-to)	1344-1352
Number of pages	9
Journal	Synthesis
Issue number	SPEC. ISS.
DOIs	https://doi.org/10.1055/s-1994-25692
State	Published - 1994

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "The self-assembly and dynamic properties of thiophene-containing [2]catenanes",

abstract = "The template-directed syntheses of two novel [2]catenanes, incorporating bisparaphenylene-34-crown-10 interlocked with tetracationic cyclophanes, containing either one or two 2,5-disubstituted thiophene residues in addition to two bipyridinium units, are reported. The X-ray crystal structures of one of these [2]catenanes and of its component tetracationic cyclophane are reported. The former exhibits short [S···O] contacts in addition to the expected π-π and [C-H···O] stabilising interactions. Dynamic 1H NMR spectroscopy has revealed that there is a substantial degree of order which characterises the molecular structures of both these [2]catenanes in solution at a noncovalent bonding level. Identifying and understanding these noncovalent bonding interactions between the molecular components are crucial to the design of catenanes that will self-assemble in a highly efficient manner.",

author = "Ashton, {P. R.} and Preece, {J. A.} and Stoddart, {J. F.} and Tolley, {M. S.} and White, {A. J P} and Williams, {D. J.}",

year = "1994",

doi = "10.1055/s-1994-25692",

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AU - Ashton, P. R.

AU - Preece, J. A.

AU - Stoddart, J. F.

AU - Tolley, M. S.

AU - White, A. J P

AU - Williams, D. J.

PY - 1994

Y1 - 1994

N2 - The template-directed syntheses of two novel [2]catenanes, incorporating bisparaphenylene-34-crown-10 interlocked with tetracationic cyclophanes, containing either one or two 2,5-disubstituted thiophene residues in addition to two bipyridinium units, are reported. The X-ray crystal structures of one of these [2]catenanes and of its component tetracationic cyclophane are reported. The former exhibits short [S···O] contacts in addition to the expected π-π and [C-H···O] stabilising interactions. Dynamic 1H NMR spectroscopy has revealed that there is a substantial degree of order which characterises the molecular structures of both these [2]catenanes in solution at a noncovalent bonding level. Identifying and understanding these noncovalent bonding interactions between the molecular components are crucial to the design of catenanes that will self-assemble in a highly efficient manner.

AB - The template-directed syntheses of two novel [2]catenanes, incorporating bisparaphenylene-34-crown-10 interlocked with tetracationic cyclophanes, containing either one or two 2,5-disubstituted thiophene residues in addition to two bipyridinium units, are reported. The X-ray crystal structures of one of these [2]catenanes and of its component tetracationic cyclophane are reported. The former exhibits short [S···O] contacts in addition to the expected π-π and [C-H···O] stabilising interactions. Dynamic 1H NMR spectroscopy has revealed that there is a substantial degree of order which characterises the molecular structures of both these [2]catenanes in solution at a noncovalent bonding level. Identifying and understanding these noncovalent bonding interactions between the molecular components are crucial to the design of catenanes that will self-assemble in a highly efficient manner.

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IS - SPEC. ISS.

ER -

The self-assembly and dynamic properties of thiophene-containing [2]catenanes

Abstract

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